Phenylhydrazine → 9-Ethyl-3-carbazolecarbaldehyde phenylhydrazone

HRID 2250302Notes

Reaction equation

HRID 2250302 reaction equation
[C:1]1([NH:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:9]([N:11]1[C:23]2[CH:22]=[CH:21][C:20]([CH:24]=O)=[CH:19][C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH3:10]>C(O)(C)C>[C:1]1([NH:7][N:8]=[CH:24][C:20]2[CH:21]=[CH:22][C:23]3[N:11]([CH2:9][CH3:10])[C:12]4[C:17]([C:18]=3[CH:19]=2)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 820559-ethyl-9H-carbazole-3-carbaldehyde

Product 1

HCID 688623579-Ethyl-3-carbazolecarbaldehyde phenylhydrazone

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of phenylhydrazine (0.1 mole, from Aldrich, Milwaukee, Wis.) and 9-ethylcarbazole-3-carbaldehyde (0.1 mole, from Aldrich) was dissolved in 100 ml of isopropanol in a 250 ml, 3-neck round bottom flask equipped with a reflux condenser and a mechanical stirrer. The solution was refluxed for 2 hours. At the end of the reaction, as indicated by the disappearance of the starting materials using thin layer chromatography, the mixture was cooled to room temperature. The 9-ethylcarbazole-3-carbaldehyde phenylhydrazone crystals that formed upon standing were filtered off, washed with isopropanol, and dried in a vacuum oven at 50° C. for 6 hours.

Workup

  1. customequipped with a reflux condenser and a mechanical stirrer
  2. temperatureThe solution was refluxed for 2 hours
  3. customAt the end of the reaction

Sources & evidence

ORD record
ord-d9075180daf04b109d59f72907974fab
Source dataset
uspto-grants-2008_01
Patent number
US07316878B2

Reaction notes

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